Nitrocyclohexane Explained

Nitrocyclohexane is an organic compound with the molecular formula C₆H₁₁NO₂. It is a colorless liquid, but degraded samples appear pale yellow. It once was produced commercially as a precursor to caprolactam].

Preparation

It is prepared by reaction of nitrogen dioxide with cyclohexane, the so-called Nixian process.^[1] Cyclohexane is a convenient substrate because all twelve C-H bonds are equivalent, so mononitration does not give isomers (unlike the case of n-hexane).^[2]

Hazards

Nitrocyclohexane is highly flammable and a strong oxidizing agent. It is listed as an extremely hazardous substance by the Emergency Planning and Community Right-to-Know Act, and the NOAA warns that it can be explosive.^[3]

Further reading

• 75 . 16 . 4047 . 1953 . 10.1021/ja01112a049 . Iffland . Don C. . Criner . G. X. . Preparation of Nitro Compounds from Oximes. II. The Improved Synthesis of Nitrocycloalkanes. Journal of the American Chemical Society .
• Synthesis of 1-Benzylnaphthalenes . The Journal of Organic Chemistry . 25 . 10.1021/jo01076a605 . 1960 . 6 . 1040–1041 . Fahim . Hussein . Fleifel . Abdallah . Fahim . Fawzia .

Notes and References

1. Book: 10.1002/14356007.a18_261.pub2 . Oxidation . Ullmann's Encyclopedia of Industrial Chemistry . 2015 . Teles . J. Henrique . Hermans . Ive . Franz . Gerhard . Sheldon . Roger A. . 1–103 . 978-3-527-30385-4 .
2. 10.1002/1521-3773(20010105)40:1<222::AID-ANIE222>3.0.CO;2-W. Efficient Catalytic Alkane Nitration with NO2 under Air Assisted by N-Hydroxyphthalimide. 2001. Sakaguchi. Satoshi. Nishiwaki. Yoshiki. Kitamura. Takaaki. Ishii. Yasutaka. Angewandte Chemie International Edition. 40. 222–224.
3. Web site: Cameo Chemicals - NITROCYCLOHEXANE . July 9, 2012.